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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H15N3O2S
Molecular Weight 229.3007
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ERGOTHIONEINE

SMILES

C[N+](C)(C)[C@@]([H])(Cc1cnc([nH]1)[S-])C(=O)O

InChI

InChIKey=SSISHJJTAXXQAX-ZETCQYMHSA-N
InChI=1S/C9H15N3O2S/c1-12(2,3)7(8(13)14)4-6-5-10-9(15)11-6/h5,7H,4H2,1-3H3,(H2-,10,11,13,14,15)/t7-/m0/s1

HIDE SMILES / InChI

Molecular Formula C9H15N3O2S
Molecular Weight 229.3007
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

ERGO (Ergothioneine) is naturally occurring antioxidant derived from the diet and abundantly contained in golden oyster mushroom (Pleurotus cornucopiae var. citrinopileatus. It is hydrophilic and membrane impermeable, but is well absorbed from the gastrointestinal tract due to the presence of a specific carrier‐mediated transport system, carnitine/organic cation transporter OCTN1/SLC22A4, essential for the beta-oxidation of fatty acids. Numerous in vitro assays have demonstrated the antioxidant and cytoprotective capabilities of ERGO against a wide range of cellular stressors, but an antioxidant role has yet to be fully verified in vivo. Nevertheless, the accumulation, tissue distribution, and scavenging properties, all highlight the potential for EGT to function as a physiological antioxidant. Because ERGO is highly distributed into the brain after oral ingestion, OCTN1 may contribute to the alleviation of oxidative stress and promotion of neuronal differentiation via the uptake of ERGO in the brain, perhaps abating symptoms of neurological disorders.

CNS Activity

Curator's Comment:: “Known to be CNS active in mouse. Human data not available

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q9H015
Gene ID: 6583.0
Gene Symbol: SLC22A4
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Estimation of ergothioneine in urine, blood and organs by determination of the alkaline perhydrol-labile sulfur.
1952 Oct
Patents

Sample Use Guides

in mice: To clarify the exposure of ERGO (ergothioneine) to brain and the possible antidepressant‐like effect after oral ingestion, ERGO or GOME (golden oyster mushroom extract) which contains 1.2% (w/w) ERGO was mixed with feed and provided to mice for 2 weeks, and then ERGO concentration and antidepressant‐like effect were evaluated by LC‐MS/MS and FST (forced swimming test) or TST (tail suspension test), respectively.
Route of Administration: Oral
Human OCTN1 was expressed in 293 cells. Analysis of transport efficiency of stachydrine-related solutes, affinity, and Na+ dependence indicates that the physiological substrate is ergothioneine (ET). Efficiency of transport of ET was as high as 195 μl per min per mg of protein. By contrast, the carnitine transporter OCTN2 from rat did not transport ET at all
Substance Class Chemical
Created
by admin
on Sat Jun 26 03:07:08 UTC 2021
Edited
by admin
on Sat Jun 26 03:07:08 UTC 2021
Record UNII
BDZ3DQM98W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ERGOTHIONEINE
INCI   MI  
INCI  
Official Name English
THIASINE
Common Name English
SYMPECTOTHION
Common Name English
ERGOTHIONEINE [INCI]
Common Name English
THIONEINE
Common Name English
(.ALPHA.S)-.ALPHA.-CARBOXY-2,3-DIHYDRO-N,N,N-TRIMETHYL-2-THIOXO-1H-IMIDAZOLE-4-ETHANAMINIUM INNER SALT
Common Name English
L(+)-ERGOTHIONEINE
Common Name English
ERGOTHIONEINE [MI]
Common Name English
NSC-7175
Code English
Classification Tree Code System Code
DSLD 4323 (Number of products:1)
Created by admin on Sat Jun 26 03:07:08 UTC 2021 , Edited by admin on Sat Jun 26 03:07:08 UTC 2021
Code System Code Type Description
CAS
497-30-3
Created by admin on Sat Jun 26 03:07:08 UTC 2021 , Edited by admin on Sat Jun 26 03:07:08 UTC 2021
PRIMARY
FDA UNII
BDZ3DQM98W
Created by admin on Sat Jun 26 03:07:08 UTC 2021 , Edited by admin on Sat Jun 26 03:07:08 UTC 2021
PRIMARY
ECHA (EC/EINECS)
207-843-5
Created by admin on Sat Jun 26 03:07:08 UTC 2021 , Edited by admin on Sat Jun 26 03:07:08 UTC 2021
PRIMARY
MERCK INDEX
M4990
Created by admin on Sat Jun 26 03:07:08 UTC 2021 , Edited by admin on Sat Jun 26 03:07:08 UTC 2021
PRIMARY Merck Index
RXCUI
1314350
Created by admin on Sat Jun 26 03:07:08 UTC 2021 , Edited by admin on Sat Jun 26 03:07:08 UTC 2021
PRIMARY RxNorm
MESH
D004880
Created by admin on Sat Jun 26 03:07:08 UTC 2021 , Edited by admin on Sat Jun 26 03:07:08 UTC 2021
PRIMARY
WIKIPEDIA
ERGOTHIONEINE
Created by admin on Sat Jun 26 03:07:08 UTC 2021 , Edited by admin on Sat Jun 26 03:07:08 UTC 2021
PRIMARY
PUBCHEM
5351619
Created by admin on Sat Jun 26 03:07:08 UTC 2021 , Edited by admin on Sat Jun 26 03:07:08 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR